Diary of a Sales Engineer

In Episode 36 of Diary of a Sales Engineer, Ryan and Sameer discuss how sales engineers can handle difficult prospects, skeptical buyers, technical roadblocks, and prickly internal stakeholders.They break down the difference between buyers who have been burned before, people who create roadblocks, and stakeholders who simply show up in a bad mood. The episode covers audience management, technical objections, InfoSec and architecture conversations, follow-up discipline, internal relationships with product and engineering, and how SEs can stay calm while protecting deal momentum.

Jeff Wang is the CEO of Windsurf (now part of Cognition) and a former solutions engineer who rode the SE skill set all the way to the top of one of the most high-profile AI startups in the industry. He sits down with Ryan and Sameer to talk about what that journey actually looked like.You'll hear how Jeff built automation bots that saved his teams hundreds of hours, why he started blogging about AI to land his first role in the space, and how Windsurf structured an entirely new set of engineering roles that are reshaping how companies think about presales and post-sales. We also get into what it takes to close enterprise deals when nobody knows your name, what product market fit really feels like versus what people assume, and Jeff's advice for SEs who want to build something of their own.If you're thinking about your next career move in presales, or you're curious about how the sales engineering role is evolving in the age of AI agents and forward deployed teams, this one's for you.Diary of a Sales Engineer is available on Spotify, YouTube, and Apple Podcasts.www.diaryofasalesengineer.com

Sales engineering career advice and go-to-market strategy with James Kaikis, co-founder of Pre-Sales Collective, founder of GTM Shift, and co-founder of Solution Exec and AI Sales Studio.The predictable revenue model that defined B2B SaaS for the last decade is breaking down. AI-first companies are collapsing the traditional sales cycle. Roles are merging. Swim lanes are blurring. And sales engineers are sitting in the best position to capitalize on all of it.James shares the full story behind his exit from Pre-Sales Collective, what he learned running revenue as a CRO at Testbox, and why he came back to entrepreneurship to build three businesses: GTM Shift (consulting and events for go-to-market leaders), AI Sales Studio (AI proficiency training for GTM teams), and Solution Exec (a private network for senior solutions executives). He also announces that he and Jeff Margolese are writing a book on solutions engineering.We get into the tactical stuff too. How to build a career roadmap from SE to CRO. Why lateral moves to account management or sales matter more than people realize. How to prepare for the convergence of SE, AE, CS, and professional services roles. And why the SEs who treat themselves as students of the game will be the ones who thrive in the next era of B2B.Ryan also shares his prediction on the emergence of the "account engineer" role, and we talk openly about work-life balance, setting boundaries, and being present at home while building a career in tech sales.This one is personal for us. James and the Pre-Sales Collective are the reason Ryan broke into sales engineering. 32 episodes later, here we are.If this episode hits home, send us a message. Those notes from listeners are the reason we do this.

Episode 30: You Don’t Need to Be the Most Technical Person in the RoomIn this episode, we’re joined by Alice Egan to challenge one of the biggest myths in sales engineering.The best Sales Engineers aren’t always the most technical people on the call. They’re the ones who can turn complex technical concepts into simple, compelling stories that buyers actually understand.In SaaS, this matters more than ever. Just like buying a car, most buyers don’t need to see the engine. They want to know how it works, how it fits their business, and why it solves their problem.In this episode, we discuss:Why being too technical can slow deals downHow to translate complexity into clear, buyer-friendly storiesWhen technical depth helps and when it hurtsA practical way to position yourself at the very beginning of a sales callHow top Sales Engineers read the room and adjust in real timeIf you’re a Sales Engineer, Solutions Engineer, or work in presales and feel pressure to always be the most technical voice, this episode will change how you think about your role.Tune in for real-world insights and practical nuggets you can use immediately.

In this episode of Diary of a Sales Engineer, we sit down with Yuji Higashi, founder of Better Career and co-founder of the Presales Collective, to uncover the real secrets behind building a high-earning, high-impact Sales Engineering career.We break down everything SEs wish they learned years earlier:How SE compensation actually worksCommon salary and commission split structuresLeveling frameworks and what separates junior, mid, and senior SEsHow to position yourself for the role you really wantHow to land roles you didn’t think you were qualified forWhat companies look for when hiring top technical talentYuji brings a unique perspective from coaching hundreds of SEs, analyzing comp bands across the industry, guiding people into roles they didn’t think they could land, and helping them negotiate offers that transform their careers.Whether you’re trying to break into Sales Engineering, get promoted, or maximize your earning potential, this conversation is packed with real-world, actionable insights.If you want to understand your value as an SE and learn how to take control of your career, this is an episode you won’t want to miss.

Feeling overwhelmed by too much on your plate? In this episode, we break down how to strategically prioritize when everything feels urgent. We talk about why the biggest deal isn’t always the most important, how to zoom out and assess impact, and how to create mental clarity when you’re drowning in tasks.Whether you’re in presales, sales, or any high-stakes role, this one’s about learning to breathe, focus, and make smart choices when the pressure’s on.👉 Tune in to learn how to work smarter — not just harder.

Confidence can make or break a deal. In this episode, we unpack how to push back without sounding defensive, why saying “it depends” can quietly kill your credibility, and how to replace it with clear, confident answers that move the conversation forward. We also dig into the value of sharing real stories of what’s worked for other customers so prospects see you as a trusted partner, not just another vendor.

In this episode, Sameer and Ryan discuss the often-overlooked part of the sales engineering role: training and enablement.They talk about why SEs need to be just as skilled at running internal and external trainings as they are at giving demos. From handling live sessions with dozens of attendees to managing questions, chat, and content flow, this episode highlights how great SEs make it all look easy.The conversation was inspired by a real-life moment where a Presales Director paused a call to shout out Sameer in front of the entire team for leading a world-class session.

In this milestone 20th episode of Diary of a Sales Engineer, we sit down with Arvi Carkanji, a seasoned recruiter who has helped countless solutions engineers navigate the job market. From landing your first role to making strategic career moves, Arvi shares what she really looks for when hiring, what makes candidates stand out, and the red flags that send applications straight to the “no” pile.

In this episode Ryan, Sameer, and Chris discuss the best habits for sales engineers.

In this episode, Ryan and Sameer discuss Ryan’s experience during his first 30 days at a new company. They share key insights, practical tips, and strategies to help you navigate the critical first month in a new role. From building your internal brand to setting yourself up for long-term success, they cover what works, what doesn’t, and what you should prioritize. Tune in for actionable advice on making the most of your first 30 days!

In this episode, we chat with Aidan Brannigan about how he amassed over 400 million views through engaging content. Learn what makes a great meme, how to create content that resonates, and tips for selling your product or service through storytelling. Don't miss these actionable insights to level up your sales and content game!

In this episode, Sameer and Ryan are joined by none other than John Care, one of the most influential voices in Sales Engineering. Together, we explore how the role of SEs has evolved over the years and dive into how AI is poised to reshape the future of our profession. From insights into where SEs have been to bold predictions about where we’re headed, this is a conversation you don’t want to miss!